Strategic Technology Leadership for Growing Businesses
I’m Jamie Taylor, a Fractional CTO and technology consultant with over 20 years of experience helping businesses navigate complex technology challenges and achieve their strategic goals. RJJ Software has evolved from a hands-on development consultancy into a strategic technology advisory practice, reflecting my transition from building solutions to guiding organisations through technology transformation and growth.
Whilst I still maintain deep technical expertise—and occasionally contribute to implementation work—my primary focus is now strategic consulting: fractional CTO services, technology due diligence, architecture reviews, and engineering leadership development. This shift allows me to deliver greater business impact by focusing on the decisions and strategies that drive long-term success.
As a Microsoft MVP, creator of OwaspHeaders.Core (with over 1.5 million downloads), and host of The Modern .NET Show (170+ episodes), I bring both technical depth and strategic perspective to every engagement. My experience spans startups navigating rapid growth, established companies undergoing digital transformation, and investors making critical technology decisions.
Core Consulting Services
⚡ Fractional CTO Services: Senior Technology Leadership, Flexible Engagement
Get the strategic technology guidance you need without the full-time executive cost. Perfect for startups and SMEs navigating critical growth phases or technology transformations.
What you get:
- Strategic technology roadmap development aligned with business goals
- Vendor management and technology procurement guidance
- Team mentorship, capability building, and hiring support
- Board-level reporting and investor communications
- Technology budget planning and optimisation
- Critical decision-making support during pivotal moments
Engagement Model: 2-4 days per month, retained basis
Ideal Client: Startups and SMEs (10-100 employees) experiencing rapid growth, undergoing technology transformation, or needing strategic guidance without full-time CTO cost. Often venture-backed or preparing for Series A/B funding rounds.
🔍 Technology Due Diligence: Make Technology Decisions with Confidence
Independent technical assessment for investors, acquirers, or leadership teams evaluating technology systems, teams, and strategies. Deliver clarity and confidence for high-stakes decisions.
What you get:
- Comprehensive codebase and architecture assessment
- Technology stack evaluation and risk identification
- Technical team capability and culture analysis
- Scalability and technical debt quantification
- Security posture and compliance review
- Detailed report with risk ratings and recommendations
Engagement Model: 1-2 weeks, fixed price
Ideal Client: Private equity firms, venture capital investors, or companies considering acquisitions. Also suitable for leadership teams seeking independent validation before major technology investments or transformations.
🛡️ Architecture & Security Reviews: Identify Risks and Optimisation Opportunities
Comprehensive technical assessment of your systems, focusing on architecture quality, security posture, and performance optimisation. Receive actionable recommendations to reduce risk and improve reliability.
What you get:
- Architecture pattern analysis and improvement recommendations
- Security vulnerability assessment and remediation roadmap
- Performance bottleneck identification and optimisation strategies
- Code quality review with technical debt quantification
- Infrastructure and deployment pipeline evaluation
- Prioritised action plan with effort estimates
Engagement Model: 1-2 weeks, fixed price
Ideal Client: Established businesses (50+ employees) experiencing scaling challenges, preparing for compliance certification, or addressing security concerns. Often triggered by performance issues, security incidents, or growth milestones.
📋 Technology Strategy Workshops: Align Technology with Business Goals
Facilitated sessions bringing together leadership, technology teams, and stakeholders to create actionable technology strategies. Transform ambiguous objectives into clear roadmaps.
What you get:
- Pre-workshop discovery and stakeholder interviews
- Facilitated strategy sessions with leadership and technical teams
- Technology roadmap development with prioritised initiatives
- Build vs. buy analysis for key capabilities
- Cost modelling and resource planning
- Post-workshop documentation and implementation guidance
Engagement Model: Half-day to 2-day sessions, fixed price
Ideal Client: Companies at strategic inflection points: product pivots, market expansion, digital transformation initiatives, or leadership transitions. Works best when stakeholders are aligned on the need for strategic clarity.
👥 Engineering Leadership Development: Build High-Performing Technical Teams
One-on-one coaching and team development programmes for technical leaders transitioning into management or scaling teams. Build leadership capabilities that drive sustainable team performance.
What you get:
- Leadership skills assessment and development planning
- Regular coaching sessions addressing real-time challenges
- Team health diagnostics and improvement strategies
- Hiring and onboarding process optimisation
- Technical decision-making frameworks
- Career development and succession planning support
Engagement Model: Flexible duration, monthly retainer
Ideal Client: CTOs, engineering managers, and technical leads managing teams of 5-50 engineers. Often experiencing rapid team growth, navigating first-time management challenges, or preparing for senior leadership transitions.
🚀 Ruby on Rails Development: Modern Web Applications at Speed
Building modern web applications, APIs, and platforms with Ruby on Rails. Ideal for startups needing rapid MVP development and established businesses modernising legacy systems.
What you get:
- Full-stack Rails application development and architecture
- API design and development (REST, GraphQL)
- Performance optimisation and scalability planning
- Rails application modernisation and upgrade strategies
- Team training and Rails best practices consulting
- Integration with modern frontend frameworks and cloud infrastructure
Engagement Model: Project-based or retained development support
Ideal Client: Startups building web platforms, SaaS companies, and established businesses needing rapid web application development. Often product-focused companies requiring fast iteration and modern, maintainable codebases.
🤖 AI Engineering & Integration: Strategic AI Implementation
Helping organisations adopt AI strategically—from workflow integration to team enablement. Deliver competitive advantage through pragmatic AI implementation.
What you get:
- AI workflow integration for existing business processes
- AI-enhanced application development and LLM integration
- Development team training on AI-assisted development tools
- R&D and skunkworks programme setup for AI exploration
- AI strategy consulting and technology selection guidance
- Proof-of-concept development and feasibility assessment
Engagement Model: Workshops (1-5 days), retained advisory, or project-based implementation
Ideal Client: Companies exploring AI adoption, development teams wanting to leverage AI tools for productivity gains, and businesses seeking competitive advantage through AI-powered features. Works across all technology stacks.
Discuss Your Technology Challenges →
Proven Expertise Across Technology & Business
Technical Depth
My technical foundation spans .NET, Ruby on Rails, cloud architecture, application security, API design, AI engineering, and developer experience optimisation. This depth ensures strategic recommendations are grounded in technical reality—avoiding ivory tower advice that fails in practice. I’ve built production systems serving millions of users, architected secure platforms handling sensitive data, and led teams through complex technical migrations.
Ruby on Rails & Modern Web Development
Building modern web applications and APIs with Ruby on Rails, I bring expertise in rapid application development, clean architecture patterns, and scalable platform design. From startup MVPs requiring fast time-to-market to established platforms needing modernisation, Rails enables pragmatic, maintainable solutions. My Ruby on Rails experience spans full-stack development, API design, performance optimisation, and team mentorship.
AI Engineering & Strategic Implementation
With the rapid evolution of AI capabilities, I help organisations navigate strategic AI implementation—from integrating AI workflows into existing business processes to training development teams on AI-assisted tooling. My AI engineering services include building AI-enhanced applications, advising on LLM integration strategies, establishing R&D programmes for AI exploration, and enabling teams to leverage AI tools effectively. The focus is on delivering measurable business value and competitive advantage through pragmatic AI adoption.
Recognition & Thought Leadership
As a Microsoft MVP, I’m recognised for technical expertise and community contribution. My open-source project OwaspHeaders.Core has surpassed 1.5 million downloads, helping thousands of developers improve application security. Through The Modern .NET Show podcast, I’ve interviewed industry leaders and shared insights from over 170 episodes. I regularly speak at conferences, contribute to technical publications, and share knowledge through writing and mentoring.
Learn More About My Background →
How We Work Together
1. Discovery Call
We discuss your challenges, goals, and determine if we’re a good fit. This 30-45 minute conversation helps me understand your specific needs and explore how strategic consulting can deliver value.
2. Proposal
I provide a detailed proposal with clear objectives, deliverables, timeline, and success metrics. You’ll know exactly what you’re getting and how we’ll measure success.
3. Delivery
We execute the engagement with regular progress updates, collaborative working sessions, and transparent communication. You stay informed and involved throughout.
4. Follow-up
Knowledge transfer ensures your team can maintain and build upon the improvements. Post-engagement support period helps answer questions and ensure long-term success.
Client Success
Jamie is an absolute Rockstar. Within a week of him working with us, he had already identified five different areas for improvement, given two inspiring talks, and created a handful of engaging demos, all leading to almost immediate ROI.
Ready to Accelerate Your Technology Strategy?
Whether you’re navigating growth, evaluating technology investments, or building high-performing teams, strategic guidance can accelerate your success and reduce risk.